Synthesis of benzimidazole based analogues of sphingosine-1-phosphate: Discovery of potent, subtype-selective S1P 4 receptor agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 19, 2004, Pages 4903-4906

  Clemens, Jeremy J ^a   Davis, Michael D ^b   Lynch, Kevin R ^b,c   Macdonald, Timothy L ^a  

^a University of Virginia   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

^c UNIVERSITY OF VIRGINIA   (United States)

Author keywords

FTY720; S1P; S1P analogues; S1P receptor agonists; S1P 4; Sphingosine 1 phosphate

Indexed keywords

ALCOHOL; BENZIMIDAZOLE DERIVATIVE; G PROTEIN COUPLED RECEPTOR; GUANINE NUCLEOTIDE BINDING PROTEIN; IMMUNOSUPPRESSIVE AGENT; LIGAND; PHOSPHATE; SPHINGOSINE 1 PHOSPHATE; SPHINGOSINE 1 PHOSPHATE RECEPTOR AGONIST; UNCLASSIFIED DRUG;

ARTICLE; BINDING ASSAY; CELL ACTIVATION; CELL MOTILITY; CELL SHAPE; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG SYNTHESIS; EMBRYO; HUMAN; HUMAN CELL; LYMPHATIC SYSTEM; METHYLATION; PROTEIN EXPRESSION; PROTEIN FAMILY; PROTEIN INTERACTION; STEREOCHEMISTRY;

BENZIMIDAZOLES; HUMANS; LYSOPHOSPHOLIPIDS; RECEPTORS, LYSOSPHINGOLIPID; SPHINGOSINE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4444316123     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.07.030     Document Type: Article

References (16)

1. For a short review on S1P as a signaling molecule, see: S. Spiegel, and S. Milstien J. Biol. Chem. 277 2002 25851
2. For a brief review on the S1P receptors, see: J. Chun, and B. Anliker J. Biol. Chem. 279 2004 20555 20558
3. For a review on S1P receptor nomenclature, see: J. Chun, E.J. Goetzl, T. Hla, Y. Igarashi, K.R. Lynch, W. Moolenaar, S. Pyne, and G. Tigyi Pharmacol. Rev. 54 2002 265
4. E.J. Goetzl, H. Lee, H. Dolezalova, K.R. Kalli, C.A. Conover, Y.L. Hu, T. Azuma, T.P. Stossel, J.S. Karliner, and R.B. Jaffe Ann. N.Y. Acad. Sci. 905 2000 177
5. N. Sugimoto, N. Takuwa, H. Okamoto, S. Sakurada, and Y. Takuwa Mol. Cell. Biol. 23 2003 1534
6. M. Maceyka, S.G. Payne, S. Milstien, and S. Spiegel BBA-Mol. Cell. Biol. L. 1585 2002 193 201
7. M. Forrest, S.-Y. Sun, R. Hajdu, J. Bergstrom, D. Card, G. Doherty, J. Hale, C. Keohane, C. Meyers, J. Milligan, S. Mills, N. Nomura, H. Rosen, M. Rosenbach, G.-J. Shei, I.I. Singer, M. Tian, S. West, V. White, J. Xie, R. Proia, and S. Mandala J. Pharmacol. Exp. Ther. 309 2004 758 768
8. M.G. Sanna, J. Liao, E. Jo, C. Alfonso, M.-Y. Ahn, M.S. Peterson, B. Webb, S. Lefebvre, J. Chun, N. Gray, and H. Rosen J. Biol. Chem. 279 2004 13839
9. M. Matloubian, C.G. Lo, G. Cinamon, M.J. Lesneski, Y. Xu, V. Brinkmann, M.L. Allende, R.L. Proia, and J.G. Cyster Nature 427 2004 355
10. M.H. Gräler, G. Bernhardt, and M. Lipp Genomics 53 1998 164
11. M.H. Gräler, R. Grosse, A. Kusch, E. Kremmer, T. Gudermann, and M. Lipp J. Cell. Biochem. 89 2003 507
12. T. Kohno, H. Matsuyuki, Y. Inagaki, and Y. Igarashi Genes Cells 8 2003 685
13. M.R. Candelore, M.J. Wright, L.M. Tota, J. Milligan, G.-J. Shei, J.D. Bergstrom, and S.M. Mandala Biochem. Biophys. Res. Commun. 297 2002 600
14. J.J. Clemens, M.D. Davis, K.R. Lynch, and T.L. Macdonald Bioorg. Med. Chem. Lett. 13 2003 3401
15. D.S. Im, J. Clemens, T.L. Macdonald, and K.R. Lynch Biochemistry 40 2001 14053
16. 35S]GTP (1200 Ci/mmol) and test lipid. After incubating for 30 min at 30°C, bound radionuclide was separated from free by filtration through Whatman GF/C paper using a Brandel Cell Harvester (Gaithersburg, MD). Bound radionuclide was detected with a Packard Top Count liquid scintillation counter